Luxury Private Southern Highlands Tour
Duration: 10 hours
From $1550.00 AUD for two guests.
Luxury Private Tour
The Southern Highlands is one of New South Wales' best-kept secrets - and one of the finest day trips from Sydney. Just 90 minutes south of the city, rolling countryside gives way to sandstone heritage villages, cool-climate vineyards, dramatic escarpment waterfalls and private farmland where kangaroos graze at dusk. This is a 10-hour private day tour designed for guests who want to experience the Australian country-side properly.
Southern Highlands Private Tour
Australia’s Best Wineries
Native Wildlife
Extraordinary walks
The Southern Highlands sits in a sweet spot that few visitors to Sydney ever reach. The air is cooler, the pace is slower, and the landscape - all emerald meadows, granite outcrops and eucalyptus ridgelines - feels a world away from the harbour. This private Southern Highlands tour takes you through the best of it: heritage villages that date to the early colonial era, acclaimed vineyards pouring some of Australia's most underrated cool-climate wines, and one of the state's great natural landmarks. It wraps up somewhere truly special — a working farm where kangaroos roam freely, untouched by the usual tourist trail.
QUINTESSENTIAL AUSTRALIAN COUNTRY-SIDE
Itinerary
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Stop 1 || Berrima
Australia's most intact Georgian village, Berrima has barely changed since the 1840s. Sandstone courthouse, colonial gaol, historic inn - and a main street of galleries, providores and cafés that make it worth lingering. It's the ideal first stop: unhurried, quietly beautiful, and a reminder that the Southern Highlands has been drawing visitors for a very long time.
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Stop 2 || Bendooley Estate
One of the Southern Highlands' most celebrated estates. The cellar door at Bendooley pours fine cool-climate wines alongside charcuterie plates and local produce - the kind of afternoon tasting that slows the day down in exactly the right way. The Book Barn next door is an institution: thousands of secondhand and rare books in a converted stone barn on a working vineyard. It's worth time on its own.
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Stop 3 || Bowral
The social and commercial centre of the Southern Highlands, Bowral is the kind of town that rewards a slow stroll. Leafy boulevards, heritage architecture, independent bookshops and some excellent cafés line the main streets. It's also home to Dirty Jane's - a sprawling antiques and vintage market beloved by locals - and Green Lane, a quiet pocket of boutiques worth finding.
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Stop 4 || Fiztroy Falls
At 81 metres, Fitzroy Falls is one of the most dramatic waterfall lookouts in New South Wales. The water drops from the Barrengarry Gorge escarpment into a deep valley of ancient rainforest below - spectacular in any season, extraordinary after rain. The Jersey Lookout offers the best vantage point and, on a clear day, views across the Kangaroo Valley all the way to the coast.
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Stop 5 || Boscobel Farm
The tour finishes somewhere most visitors to the Southern Highlands will never see. Boscobel Farm is a private working property - rolling meadows, quiet forest, absolute stillness - and it's exclusively ours for the afternoon. An afternoon in the open air, and as the day cools, the kangaroos emerge. This is the kind of ending that stays with people.
Our Guests
Frequently Asked Questions
How long is the Southern Highlands day tour from Sydney?
The tour runs for approximately 10 hours, departing from your hotel/airbnb/cruise terminal in the morning and returning in the evening. Exact departure times are confirmed at booking.
How much does the Southern Highlands tour cost?
The Private Southern Highlands Tour starts from $1,550 AUD for two guests. We can accommodate up to six guests - contact us for group pricing.
What's included in the tour?
Private luxury vehicle transport from Sydney, a knowledgeable local guide, wine tastings at Bendooley Estate, a visit to Fitzroy Falls, time in historic Berrima and Bowral, and a visit to Boscobel Farm with wild kangaroos.
Which wineries do you visit on the Southern Highlands tour?
The tour includes tastings at Bendooley Estate - known for its cool-climate wines, charcuterie and the iconic Book Barn - and Mount Ashby Estate, a refined working property with French-influenced dining.
Is this a private tour?
Yes. Every tour we run is 100% private - exclusively for your group. There are no shared coaches, no strangers, and no fixed group schedules. The itinerary moves at your pace.
Do you offer hotel pickup from Sydney?
Yes. Pickup and drop-off are included from central Sydney hotels and cruise ship terminals.
Will we see kangaroos?
Almost certainly. The tour finishes with at Boscobel Farm, where wild kangaroos roam freely across the open meadows - particularly in the late afternoon.
How far is the Southern Highlands from Sydney?
The Southern Highlands is approximately 90 minutes south-west of Sydney via the Hume Highway. It's one of the finest and most accessible day trips from the city.
Do you cater for corporate groups?
Yes. The Southern Highlands tour is perfectly suited to corporate groups, conference delegates, and executive teams. Every experience is 100% private — your group only, no shared coaches, no strangers. Groups from 2 to 14 guests welcome. To discuss a tailored package, contact Alex on +61 468 333 514 or email info@ausadventureco.com.au.
Need help deciding? Talk to an expert
We're here to help 9am – 5pm Monday to Sunday by calling +61 468 333 514, otherwise, email us anytime and we'll be in touch.